


First Times

by Mrs_Don_Draper



Category: Mad Men
Genre: F/M, First Time, Light Angst, Light-Hearted, Loss of Virginity, Some Humor
Language: English
Status: Completed
Published: 2013-07-21
Updated: 2013-07-20
Packaged: 2017-12-20 21:08:33
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 861
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/891884
Author URL: https://archiveofourown.org/users/Mrs_Don_Draper/pseuds/Mrs_Don_Draper
Summary: <blockquote class="userstuff">
              <p>How Sterling-Cooper-Draper-Pryce lost their virginity.</p>
            </blockquote>





	1. Roger Sterling {Year: 1942, Age: 20}

“Come on Jessica, I’ve been waiting and waiting. I thought you said we could when you turned eighteen,” he whined.

Jessica nervously lit a cigarette that she had stolen from her mother’s purse. She let out a cough, but forced herself to like it. All her friends smoked.

“I don’t know, Roger…My mother—”

Roger was persistent.

“I ship out in two weeks. I don’t know the next chance I’ll get.”

Jessica’s lip trembled. She hated it when he reminded her of that. Her hands trembled so badly that she dropped the cigarette.

“It’s not fair, Roger! Why do you have to go?”

She cried into her hands. Roger wrapped his arms around her, kissed her soft brown hair, memorized the way she smelled. Jessica turned around to hug him back, kissed him on the mouth. It was only a matter of time before he backed them onto her bed.

When he shipped out to Europe, she promised to always love him. 

By 1946, she was married with two kids, and Mona was pregnant with Margaret.


	2. Bertram Cooper {Year: 1935, Age: 23}

Bert Cooper has always found Asian artwork and customs to be endlessly fascinating. But no one ever really knew why. It started when he saw her at the market one day, shopping in China Town for cheaper groceries to stock up his bachelor pad. He had been picking up some vegetables for a stew when their eyes locked.

Black, black hair to match her black eyes. Purple blouse and grey skirt. Soft, white hands and a crinkle in her eyes when she smiled at him. He later found out her name was Ima Chan, but she liked it when he pronounced it Emma with a softer “e” sound.

Their visits were limited, mostly because she was already betrothed to someone her parents had picked for. Glances across chunks of meat and fruits and vegetables. Hands touching when she gave back change. An occasional “discount” on a treat, saved just for him. That is, until the one day they saw each other outside of the market.

Cooper was out with some of his friends from college, settled in at one of their favorite haunts: a tiny bar two miles from campus where booze was cheap and the food wasn't too bad either. And she was there. Smiling up at a man at the bar, then she looked over her shoulder at him, making him completely aware that she was there on purpose, and then back at the stranger again.

Something flared inside him, a mixture of pride that she had remembered where he went to school and a hatred for the man who thought he could just mosey on up to talk to her. He knocked back the rest of his drink and went to her.

“Is this man bothering you, Emma?”

He held her elbow possessively, giving the stranger a warning glare, and her eyes crinkled again.

“Why don’t you show me around your school, Bertram?”

He nodded and walked her around the large, open campus. He led her to a peaceful, man-made brook on the grounds that he liked to do his school reading by. They sat on the still-warm grass, holding hands, silent. She rested her head on his shoulder.

Then suddenly, she said, “I’ll be married soon.”

So this was good-bye then. No more hearing her tinkling laugh. No more secrets over produce. No more Emma.

He turned to look at her, took her face in his hands and kissed her. If this was to be the last time they could ever be together, he wanted to make it meaningful for both of them.


	3. Dick Whitman {Year: 1943, Age: 15}

“Come on in here, Becky. I want to show you something.”

She let out a huff, hands on hips.

“Why would I want to see your dumb barn? I have one of my own at my house.”

He grabbed her hand, tugging her along.

“Just look, ok? You’ll like it.”

Becky followed him into the barn and was delighted by what she saw. It wasn’t just Dick’s animals and tools; it was a picnic in the hayloft with a little present wrapped up on a corner of the blanket.

“Dick Whitman, you remembered my birthday!” she squealed happily.

She threw her arms around his neck and gave him a kiss on the cheek.

“Oof,” he muttered. “Well, now we’re both the same age, I guess.”

He had even made some sandwiches. There wasn’t any cake or anything to drink, but it was still the nicest thing anyone had ever done for her. She leaned over the cloth to kiss him again. Dick’s face turned red.

Becky sat back. “Did I embarrass you? I’m sor—oh…”

Her face turned red too. Dick bit his lip; he hoped Becky wouldn’t leave just because of that. He kind of wanted her to stay even more now than before.

“I’m sorry Beck. You’re just so pretty.”

And Becky, not having any other offers or prospects that were nearly as sweet or gentlemanly out in the country, decided that she did not mind one bit.


	4. Lane Pryce {Year: ????, Age: ??}

***Lane is British and felt it would be gauche to discuss his first encounter with the female flesh.***


End file.
